Diversity in the fatty-acid conformation and chain packing of cis-unsaturated lipids

Current Opinion in Structural Biology

Volumn 8, Issue 4, 1998, Pages 417-425

  Kaneko, Fumitoshi ^a   Yano, Junko ^b   Sato, Kiyotaka ^b  

^a OSAKA UNIVERSITY   (Japan)

^b HIROSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DIACYLGLYCEROL; FATTY ACID; MEMBRANE LIPID; MONOUNSATURATED FATTY ACID; OLEIC ACID; TRIACYLGLYCEROL; UNSATURATED FATTY ACID;

ARTICLE; CRYSTAL STRUCTURE; DRUG CONFORMATION; INFRARED SPECTROSCOPY; PRIORITY JOURNAL; X RAY DIFFRACTION;

EID: 0032142913     PISSN: 0959440X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0959-440X(98)80117-6     Document Type: Article

References (45)

1. Gennis RB. Biomembranes: Molecular Structure and Function. 1989;New York, Springer-Verlag.
2. Small DM. The physical chemistry of lipids. From alkanes to phospholipids. Hanahan DJ. Handbook of Lipid Research. 4:1986;233-284 Plenum Press, New York.
3. Small DM. Lateral chain packing in lipids and membranes. J Lipid Res. 25:1984;1490-1500.
4. Wang G, Lin H-N, Li S, Huang C-H. Phosphatidylcholines with sn-1 saturated and sn-2-cis monounsaturated acyl chains. Their melting behavior and structures. J Biol Chem. 270:1995;22738-22746.
5. Huang C-H, Lin H-N, Wang G. Influence of the positions of cis double bonds in the sn-2-acyl chain of phosphatidylethanolamine on the bilayer's melting behavior. J Biol Chem. 272:1997;21917-21926.
6. Barton PG, Gunstone FD. Hydrocarbon chain packing and molecular motion in phospholipid bilayers formed from unsaturated lecithins. Synthesis and properties of sixteen positional isomers of 1,2-dioctadecenoyl-sn-glycerol-3-phosphorylcholine. J Biol Chem. 250:1975;4470-4476.
7. Applegate KR, Glomset JA. Effect of acyl chain unsaturation on the packing of model diacylglycerols: a computer modeling study. J Lipid Res. 32:1991;1635-1644.
8. Applegate KR, Glomset JA. Effect of acyl chain unsaturation on the packing of model diacylglycerols in simulated monolayers. J Lipid Res. 32:1991;1645-1655.
9. Pascher I. The different conformations of the glycerol region of crystalline acylglycerols. Curr Opin Struct Biol. 6:1996;439-448.
10. Pascher I, Lundmark M, Nyholm P-G, Sundell S. Crystal structures of membrane lipids. Biochim Biophys Acta. 1113:1992;339-373.
11. Suzuki M, Ogaki T, Sato K. Crystallization and transformation mechanisms of α, β and γ polymorphs of ultra-pure oleic acid. J Am Oil Chem Soc. 62:1985;1600-1604.
12. Kobayashi M, Kaneko F, Sato K, Suzuki M. Vibrational spectroscopic study on polymorphism and order-disorder phase transition in oleic acid. J Phys Chem. 90:1986;6371-6378.
13. Suzuki M, Sato K, Yoshimoto N, Tanaka S, Kobayashi M. Polymorphic behavior of erucic acid. J Am Oil Chem Soc. 65:1988;1942-1947.
14. Sato K, Yoshimoto N, Suzuki M, Kobayashi M, Kaneko F. Structure and transformation in polymorphism of petroselinic acid (cis-ω12-octadecenoic acid). J Phys Chem. 94:1990;3180-3185.
15. Yoshimoto N, Suzuki M, Sato K. Polymorphic transformation in asclepic acid (cis-ω7-octadecenoic acid). Chem Phys Lipids. 57:1991;67-73.
16. Yoshimoto N, Nakamura T, Suzuki M, Sato K. Physical properties of binary mixtures of petroselinic acid/oleic acid and asclepic acid/oleic acid. J Phys Chem. 95:1991;3384-3390.
17. Inoue T, Motoda I, Hiramatsu N, Suzuki M, Sato K. Phase behavior of binary mixtures of cis-monounsaturated fatty acids with different ω-chain length. Chem Phys Lipids. 63:1992;243-250.
18. 1 phase of erucic acid. Acta Crystallogr C. 48:1992;1060-1063.
19. Kaneko F, Kitagawa Y, Matsuura Y, Sato K, Suzuki M, Kobayashi M. Structure of the low-melting phase of petroselinic acid. Acta Crystallogr C. 48:1992;1054-1057.
20. Kaneko F, Kobayashi M, Kitagawa Y, Matsuura Y, Sato K, Suzuki M. Structure of the high-melting phase of petroselinic acid. Acta Crystallogr C. 48:1992;1057-1060.
21. Inoue T, Motoda I, Hiramatsu N, Suzuki M, Sato K. Phase behavior of binary mixture of palmitoleic acid (cis-9-hexadecenoic acid) and asclepic acid (cis-11-octadecenoic acid). Chem Phys Lipids. 66:1993;209-214.
22. 1 and γ → α reversible solid state phase transitions. Spectrochim Acta A - Mol Biomol Spectrosc. 50:1994;1589-1603.
23. 1 reversible solid-state phase transitions of erucic acid. J Phys Chem. 100:1996;9138-9148.
24. Kaneko F, Yamazaki K, Kitagawa K, Kikyo T, Kobayashi M, Sato K, Suzuki M. Structure and crystallization behavior of the β phase of oleic acid. of outstanding interest J Phys Chem B. 101:1997;1803-1809 This paper dramatically demonstrates how the chain packing olefinic conformation and chain-length structure of the most stable β form of oleic acid can deviate from those of the other cis-monounsaturated fatty acids previously reported in [18-20].
25. Sato K, Yano J, Kawada I, Kawano M, Kaneko F, Suzuki M. Polymorphic behavior of gondoic acid and phase behavior of its binary mixtures with asclepic acid and oleic acid. J Am Oil Chem Soc. 74:1997;1153-1159.
26. Di L, Small DM. Physical behavior of the mixed chain diacylglycerol, 1-stearoyl-2-oleoyl-sn-glycerol: difficulties in chain packing produce marked polymorphism. J Lipid Res. 34:1993;1611-1623.
27. Di L, Small DM. Physical behavior of the hydrophobic core of membranes: properties of 1-stearoyl-2-linoleoyl-sn-glycerol. Biochemistry. 35:1995;16672-16677.
28. Goto M, Honda K, Di L, Small DM. Crystal structure of a mixed chain diacylglycerols, 1-stearoyl-3-oleoyl-glycerol. J Lipid Res. 36:1995;2185-2190.
29. Kodali DR, Atkinson D, Redgrave TG, Small DM. Structure and polymorphism of 18-carbon fatty acyl triacylglycerols: effect of unsaturation and substitution in the 2-position. J Lipid Res. 28:1987;403-413.
30. Sato K, Arishima T, Wang ZH, Ojima K, Sagi N, Mori H. Polymorphism of POP and SOS. I. Occurrence and polymorphic transformation. J Am Oil Chem Soc. 66:1989;664-674.
31. Engstrom L. Triglyceride systems forming molecular compounds. J Fat Sci Technol. 94:1992;173-181.
32. Koyano T, Hachiya I, Sato K. Phase behavior of mixed systems of SOS and OSO. J Phys Chem. 96:1992;10514-10520.
33. Yano J, Ueno S, Sato K, Arishima T, Sagi N, Kaneko F, Kobayashi M. FT-IR study of polymorphic transformations in SOS, POP, and POS. J Phys Chem. 97:1993;12967-12973.
34. 13C Cross-polarization and magic-angle spinning nuclear magnetic resonance of polymorphic forms of three triacylglycerols. J Am Oil Chem Soc. 73:1996;1567-1572.
35. Ueno S, Minato A, Seto H, Amemiya Y, Sato K. Synchrotron radiation X-ray diffraction study of liquid crystal formation and polymorphic crystallization of SOS (sn-1,3-distearoyl-2-oleoyl glycerol). of special interest J Phys Chem B. 101:1997;6847-6854 This paper reveals for the first time the occurrence of thermotropic liquid-crystalline phases in SOS using time-resolved synchrotron X-ray diffractometry.
36. Minato A, Ueno S, Smith K, Amemiya Y, Sato K. Thermodynamic and kinetic study on phase behavior of binary mixtures of POP and PPO forming molecular compound systems. J Phys Chem B. 101:1997;3498-3505.
37. Minato A, Ueno S, Yano J, Smith K, Seto H, Amemiya Y, Sato K. Thermal and structural properties of sn-1,3-dipalmitoyl-2-oleoylglycerol and sn-1,3-dioleoyl-2-palmitoylglycerol binary mixtures examined with synchrotron radiation X-ray diffraction. J Am Oil Chem Soc. 74:1997;3498-3505.
38. Minato A, Yano J, Ueno S, Smith K, Sato K. FT-IR study on microscopic structures and conformations of POP-PPO and POP-OPO molecular compounds. Chem Phys Lipids. 88:1997;63-71.
39. Kobayashi M. Vibrational spectroscopic aspects of polymorphism and phase transition of fats and fatty acids. Gart N, Sato K. Crystallization and Polymorphism of Fats and Fatty Acids. 1988;139-187 Macel Dekker, New York.
40. Sato K. Polymorphism of pure triacylglycerols and natural fats. Padley F. Advances in Applied Lipid Research. 2:1996;213-268 JAI Press Inc, London.
41. Ueno S, Suetake T, Yano J, Suzuki M, Sato K. Structure and polymorphic transformations in elaidic acid (trans-ω9-octadecenoic acid). Chem Phys Lipids. 72:1994;27-34.
42. Sato K, Kobayashi M. Structure, stability and crystal growth of polymorphs and polytypes of long-chain aliphatic compounds. Karl N. Crystals. 1991;65-108 Springer-Verlag, Heidelberg.
43. 2 progression bands of saturated monoacid triacylglycerols. of special interest J Phys Chem B. 101:1997;8112-8119 See annotation [44].
44. 2 progression bands of a series of monoacid triacylglycerols (TAGs) [43] and the analysis of the molecular structures of saturated mixed-acid TAGs [44].
45. Mendelsohn R, Liang GL, Strauss HL, Snyder RG. IR spectroscopic determination of gel state miscibility in long-chain phosphatidylcholine mixtures. Biophys J. 69:1995;1987-1998.